I've had iCloud integration since forever, the drill was when your auth expired you'd remove the intergration, delete the icloud storage from the filesystem restart HA, reauth (with main password) and it would start to work.
Recently a couple of versions ago, it stopped needing me to that and just a reauth (main password) started to work although it would still pop up and give me the Apple 2FA, HA did not ask for that token.
I just upgraded to 2026.5.4 and after the reboot it needed me to reauth again (which is normal after a reboot) -- however this time it is asking for the 2FA but iPhone or Macbook is not popping the 2FA dialog anymore.
I tried a normal reboot
I tried a delete-integration, delete the icloud storage
I tried using an app-specific password (with the dashes, and without the dashes)
None of it worked. Since I don't see any other posts about it, I'm assuming it's me doing something or not doing something? Help would be appreciated.
OS Version: Home Assistant OS 17.3
Home Assistant Core: 2026.5.4